By semi-popular demand, the sequel to "If You Can't Beat 'Em"! Thanks to everyone who favorited and/or reviewed! :)
Join 'Em
Dean lies to Sam a little and tells him he thinks one of them should stay at the convention for its second day ("How do they squeeze two days out of this?"). Really, Dean is pretty positive there is no angelic recruitment going on, but he wants to be separate from Sam for a little while anyway. For reasons.
And they can't both stay, he continues to lie, because there's this really sketchy activity going on in Maine. ("Uh. Which part of Maine?" Sam asks. "All of it," Dean tells him grimly. "Uh… okay. What kind of activity? Demon? Angel?" "Neither. Or both. I don't know, Sam, it's just sketchy.")
So Dean elects to stay, which makes Sam give him the strangest look in his arsenal of strange looks, but Dean shrugs innocently and tells Sam as he tosses him the Impala keys that if Baby has a single scratch when he gets back, Dean will take away his WiFi and make him babysit Crowley for three hours. ("Dean, you can't just take away WiFi—" "Watch me.")
As soon as the Impala purrs away, taking Sam's suspicious looks and stupid friggin' Destiel keychain with it, Dean sends a short, simple prayer to Cas. Vermillion, Ohio. Hotel 6. Room 211. Urgent.
He feels a little guilty tacking "urgent" on to the end of it when Cas has no wings and will probably be worried that something bad is happening, but Cas has a tendency not to answer Dean's prayers, so he figures that if anything's going to get the angel's ass moving, it'll be the suggestion that Dean's in trouble. What a way to begin wooing the guy. Dean stops in horror with his hand on the hotel exit door. Wooing Cas. Did he really just think about wooing another man? Dean Winchester does not woo, he seduces with his charming wit and devastatingly good looks!
But if wooing is what it takes, he relents, then wooing he shall do. But first he's going to need alcohol. So much alcohol.
Okay, so maybe he should technically be sticking around the hotel so he can keep an eye on the whole angel situation, since that's what he told Sam to get his nosy and interfering brother out of the way, but if he sees one more person in a tan trench coat and a fake halo, he's going to strangle them. He does at one point see a girl in Castiel get-up with her arm around the waist of another girl who Dean suspects is supposed to dressed as… him. He marvels again at the idea that there are people who actively want him and Cas to secretly be having all kinds of kinky interspecies sex. He wonders how much time and energy people put into that kind of activity. He hopes they save it all for dressing up and going to this one convention, but he kind of doubts it.
In any case, Dean abandons his post and goes to the nearest bar he can find. It's not even noon, so he's not surprised that most of them are closed. He finds one crappy day-bar that serves beer that tastes like ground-up boots, but Dean dutifully chugs down a pint and then has to stop because a) it's truly, horribly awful, and b) he doesn't want to be a drunk idiot or a hung-over mess when he finally talks to Cas.
In the end he decides to just go back to the convention and endure it for a few more painful hours, if only to ease his conscience. Again, no suspicious winged persons, but he does learn that Sam's dick is apparently a bad luck charm, and that Chuck once described Dean's voice as "a low gravelling that warns of how dangerous he is, but still capable of softness and warmth." That's the dumbest thing Dean has ever heard, and now he's annoyed and slightly pissed off again. He stays for the whole thing, though, which ends at 6:00 pm with a round of enthusiastic applause.
He doesn't know where Cas was when he called him, but he doubts he was close enough to be here by now. It's so inconvenient, having a broken angel. He's used to Castiel at his beck and call. It's rather rude of the guy to lose his wings just when Dean has an urgent revelation that heavily involves him. Dean broods over this while he stomps back to his room, ready for the bottle of Jack waiting for him in the mini fridge. He slides his key card, jerks open the door, and—
And there is the real Cas, tan trench coat and blue tie that almost matches his tie but can't quite. He is sitting at the foot of the bed Sam slept in last night until he hears the door open. "Dean!" he exclaims, as much as Cas ever really exclaims anything. He strides to the doorway, where Dean still stands somewhat stupefied. "What's going on? You said it was urgent, yet I've been sitting here for an hour, and you wreak of alcohol."
Dean is shocked by the crossness in Cas's voice. "You don't get to be angry!" he says indignantly. "I'm angry!" The wooing is not going very well, he feels.
"Why are you angry?" Cas demands. "You're the one who called to me and then left me here to wonder where you were and whether you were in danger. Tell me, Dean, why was it so urgent for me to come here if you were going to spend all day drinking and looking for women who want to have sex with you?"
"Because I'm gay for you, damn it!" Dean snaps, and then freezes in horror over what he just said. So much for wooing.
Cas cocks his head to the side, and damn it, Dean does not think it's cute, it's annoying and definitely cheating. "You… you have feelings for me? Beyond our platonic friendship, that is?"
Dean winces. "Yeah, Cas, I guess I do. Big gay crush feelings. And you wanna know the best part? Apparently every other son of a bitch on the planet that's heard of us knew about it before I did."
"I don't understand," Cas says, frowning.
"Let's just say Sam scarred me for life. We can save the whole story for later," Dean tells him. "I've got a better idea for right now." And he lets the door fall shut behind him in favor of grabbing fistfuls of Cas's trench coat and kissing him.
Sex with Cas is awkward. Between tripping out of his clothes, the mumbled "I—I'm sorry, I've only done this once," and the uncertainty over where to put his hands, it's probably the most awkward sex Dean has ever had.
He's hardly Mr. Experience here himself. Sure, he's slept his way across most of the country, but he's always been very specific about which half of the population he's whoring around with. This—flat planes, stubbly cheeks, and, well, a vastly different view between the legs—is entirely new to him.
But Dean just presses them together, touching every inch he can with his hands and his mouth, and when they've both come down from the high and can breathe normally again, Dean finds there's something a little more satisfying about this than dragging some chick home from the bar. Sex is still fantastic no matter what, but even though this was quick ("C'mon, it's your second lay, and I wasn't that far behind," Dean reassures Cas, kissing his flaming cheeks), it's the best Dean's had since… Well, since Lisa.
Cas isn't just some Big Gay Awakening, Dean knows. He's not a one-off that's going to push Dean into the world of quickies in bathrooms at gay bars; he's what Lisa once was to him. Maybe more, even, he thinks, gulping.
"Dean," Cas mumbles into Dean's chest. They're still lying one on top of the other, Dean too blissed-out to move, Cas apparently too content perched on top of him. "I'm really glad your brother—to use your words—'scarred you for life.'"
Dean laughs and curls his arms up around Cas's waist. He has this horrible feeling that when he tells Cas about Destiel, he's going to want a keychain of his own, and maybe, God forbid, he'll even want to go to that convention someday, where Dean will once again want to kill everyone in sight, but he's pretty sure that if Cas wants to read every Supernatural book in the market and attend every Destiel panel across the globe (even if that means flying—and that thought is what tells Dean he's really got it bad), then Dean will probably go along with a big damn smile on his face.
"Yeah," he says, "me too," and falls sleep with Cas on top of him.